Hexane → N-[2-Ethyl-6-(3-oxo-6-phenyl-1-hexenyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 1734875ノート

反応式

HRID 1734875 の反応式
[H-].[Na+].CCCCCC.C(OP([C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([CH2:23][CH2:24][CH2:25][C:26](=[O:28])[CH3:27])[CH:22]=1)(OCC)=O)C.[CH2:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=O)[C:32]=1[NH:39][C:40](=[O:56])[CH2:41][CH:42]1[C:55]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[O:49][C:48]2[C:43]1=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH3:30]>CN(C)C=O>[CH2:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=[CH:27][C:26](=[O:28])[CH2:25][CH2:24][CH2:23][C:21]2[CH:22]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:32]=1[NH:39][C:40](=[O:56])[CH2:41][CH:42]1[C:55]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[O:49][C:48]2[C:43]1=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH3:30]

参加物

6

反応物 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 199659985-Diethoxyphosphoryl-1-(4-oxopentyl)benzeneHCID 19966259N-(2-ethyl-6-formylphenyl)-2-(9H-xanthen-9-yl)acetamide

生成物 1

HCID 54326645N-[2-Ethyl-6-(3-oxo-6-phenyl-1-hexenyl)phenyl]-2-(9H-xanthen-9-yl)acetamide収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

49 mg (1.13 mmol) of sodium hydride (as a 55% w/w suspension in mineral oil) were washed twice, each time with hexane, and were suspended in 6 ml of dimethylformamide. 2 ml of a dimethylformamide solution containing 289 mg (0.97 mmol) of 5-diethoxyphosphoryl-1-(4-oxopentyl)benzene were added to the suspension, whilst ice-cooling. The reaction mixture was then immediately allowed to return to room temperature, after which it was stirred for 30 minutes. 300 mg (0.808 mmol) of N-(2-ethyl-6-formylphenyl)-2-(9H-xanthen-9-yl)acetamide were then added to the reaction mixture, once again whilst ice-cooling. The mixture was then stirred for 1 hour at the ice-cooling temperature and then for 3 hours at room temperature. At the end of this time, the reaction solution was poured into ice-water and extracted with diethyl ether. The organic extract was washed with water. The solvent was removed by distillation under reduced pressure, and the resulting residue was recrystallized from a mixture of methylene chloride and diethyl ether, to give 220 mg (yield 53%) of the title compound as crystals, melting at 168°-170° C.

後処理

  1. additionwere added to the suspension, whilst ice-
  2. temperaturecooling
  3. customto return to room temperature
  4. temperaturecooling
  5. temperaturecooling temperature
  6. waitfor 3 hours at room temperature
  7. extractionextracted with diethyl ether
  8. extractionThe organic extract
  9. washwas washed with water
  10. customThe solvent was removed by distillation under reduced pressure
  11. customthe resulting residue was recrystallized from a mixture of methylene chloride and diethyl ether

出典と根拠

ORDレコード
ord-6a1f8d48638e46b2b4056f044f3aa35a
出典データセット
uspto-grants-1996_07
特許番号
US05534529

反応ノート

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